I have wanted to visit Santorini for what feels like FOR.E.VER (said in booming Sandlot voice for full effect). Last fall, I finally made it happen and, happily, the trip was just as much of a dream as I always hoped it would be. In fact, I might run out of glowing adjectives by the time I get to the end of this post (to say nothing of all the other posts I have to write about my time there!)
I deliberately chose to go at the very end of October, in the last week of the tourist season (in fact, most hotels on Santorini shuttered their doors for winter the very Monday after I departed!). So what does it mean to visit Santorini in the shoulder season and why did I want to go then? Well, it’s not piping hot, and lying on the beach all day and taking dips in the ocean is probably not on the menu. But, as a very pale person, I don’t need to lie on a beach all day, and I was drawn to one huge, huge plus of shoulder season: fewer crowds. In any destination, I think that’s a good thing, but in Santorini, with its sun dappled, Pinterest perfect, tourist magnet villages, this is a BIG win. If a bit of mild chilliness in the evenings (emphasis on mild) is the only price to pay for more peace and quiet, I will gladly pony up! And guess what? I adored my time on Santorini.
I decided to split my week on Santorini in half, spending the first part in the town of Imerovigli (which is relatively quiet) and the second part in Oia (which is where all the tourists go). I loved this strategy as well, as it allowed me to explore several sides to the island.
In Imerovigli, I stayed at the Absolute Bliss Suites. While both of my hotels in Santorini were a bit more than I typically spend, another advantage of shoulder season was that their prices were at the lowest of the year when I went. And so, in Imerovigli, I decided to really go for it, springing for a suite with its own private balcony and hot tub. My four days there basically felt like one gigantic, luxurious, treat yo self moment.
My days at Imerovigli were wonderfully low-key which, after a busy fall at work, was exactly what I wanted. I made a few jaunts outside of town, going on a hike to Fira and joining a wine tour one afternoon (more on both later), but for the most part, I stayed in the comfort of my own suite. I ordered room service, I spent hours in my hot tub, I read multiple books, and I watched sunsets from start to finish. It was perfect, and it felt like a true vacation.
The Bottom Line: Oia is where everybody flocks in Santorini, and not without good reason. However, spending time in Imerovigli is definitely worth it, especially if you are looking for true relaxation. I felt like Absolute Bliss truly lived up to its name!